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Oligopyrrole macrocycles are synthetic compounds containing four or more pyrrole or pyrrole-like heterocyclic subunits within their macrocyclic frameworks. Inspired in part by the porphyrins and other tetrapyrrolic natural products, this class of compounds has evolved to include expanded porphyrins, calixpyrroles, calixphyrins, and a wide range of systems built up from bipyrrole, bis(pyrrolyl)benzene, biimidazole, or other preformed heterocyclic subunits. It has also come to encompass acyclic- and bicyclic systems. In this lecture, recent synthetic advances from the Austin group will be detailed, as will be fundamental studies designed to probe the utility of oligopyrrole macrocycles, including representative systems 1-6, as receptors for cations, anions, and, in certain cases, neutral substrates. The results of collaborative studies, focused on the testing of several “lead compounds” in various applications ranging from separation science to anticancer drug development, will also be presented. A summary of newer work, targeting the use of oligopyrrole macrocycles as liquid crystals, will likewise be included. Several lead references are listed below.
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KCS